


Don't You Cry No More (Carry On My Wayward Son)

by I_Am_Iron_Man



Category: Supernatural, Supernatural RPF
Genre: Alternate Universe - Human, Alternate Universe - Not Angels/Not Demons, Alternate Universe - Not Hunters, BDSM, Bondage, Brotherly Love, Brotherly feels, Crowley Being an Asshole, Crowley can be a douchebag, Dean Lies, Dean is 21, Dean is Not Oblivious, Dean is a Tease, Everybody is Bad at Feelings, F/M, FUCK THATS A SHIT TON OF TAGS HOLY CRAP, Gen, Hella lot of that Plot, Jail Time- Not Mail Time, Lucifer & Sam Winchester Friendship, M/M, Michael Needs a Hug, Michael has a "unrequited" crush.., Multi, My First Fanfic, Non Canonical, Not Beta Read, Not Canon Compliant, Orphans, Porn With Plot, Prisoner Dean, Prisoner Sam, Prostitution, Resist of Arrest, Running into People at Bad Times, Sam Believes Him, Sam feels bad b/c of Dean, Sam is 17, Secrets, Sick Sam Winchester, Sleeping in the Impala, Some Humor, Street Rat!Adam Milligan, Street Rats, Sweet Castiel, Threesome - M/M/M, Would Somebody Please Smack Some Sense Into Lucifer??, begging for money
Language: English
Status: In-Progress
Published: 2014-12-07
Updated: 2015-01-04
Packaged: 2018-02-28 11:58:34
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 4
Words: 2,101
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2731637
Author URL: https://archiveofourown.org/users/I_Am_Iron_Man/pseuds/I_Am_Iron_Man
Summary: <blockquote class="userstuff">
              <p>Sam and Dean are sort of street-rats, who have been living in their dad's old '67 Chevy Impala.</p><p>Their parents are dead, they have no money, and- to make things worse- Sam is almost positive that Dean is prostituting himself so that he and Sam can eat every other day.</p><p>But what is he supposed to do?</p>
            </blockquote>





	1. The Crisp Twenty

**Author's Note:**

> Title taken from KANSAS' song, "Carry On Wayward Son", which I absolutely adore.
> 
> This is a Non-Canonical Supernatural Fic.
> 
> (There looks like there's a whole fuck ton of sexy times happening during this, but really- It's a fuck ton of plot with some sexy times mixed in... sorry if you were looking for that.)
> 
> I'mma try to update weekly, but… no promises! I will definitely try, though.

**Summary for the Chapter:**

> The brothers Sam and Dean sit on the corner of the coffee shop hoping to earn some money from some pedestrians.

The two brothers sat in front of a coffee shop on the cold cement. They had been there for roughly an hour and had only gotten a dollar- which was not nearly enough to buy the large black coffee. (Which cost approximately $2.80.)

"Y'know, there _is_ another way." Dean said tiredly, rubbing his eyes with his fingers. " _Probably._ "

Sam looked at him warily. "What'd you mean?"

" _I mean_ , give me an hour and I can get us fifty bucks. Don't ask me stupid questions, Sammy." Dean answered.  
It was times like these that he wished his parents were around, so that he and Sam didn't have to be beggars and sleep in the car.

At age four, his mother passed away from breast cancer, leaving he and Sam to be raised by their alcoholic father- who was never around. When he was around, he would abuse the boys physically and emotionally.

So when Dean had turned eighteen, he packed his backpack and took Sam -whom was fourteen (and up to Dean's eyebrows)- and headed off into the world.

They left behind terrible memories and an alcoholic father who, only months after they left, had drunken himself into oblivion.

"-ean. Dean. _Hello_ , is anybody home?" Sam said, waving his hand in front of Dean's face.

Dean jumped- returning from his thoughts. " _God_ \- don't _do_ that, Sammy you scared the bejesus out of me!"

"Dude, I've been doing it for about, three minutes." Sam said, rolling his eyes. "What were you even _thinking_ about?"

"Life," Dean said wistfully. "Liberty. The pursuit of hot beverages."

Sam looked at him, and then turned to look at the sidewalk. "Okay."

"What?"

Sam stared down at his hands, feeling remorseful for himself. "Nothing."

"Yeah. _Sure._ " Dean replied.

Rather than dragging the moment out, Sam decided to be frank with Dean. He knew that Dean was either hiding something or he was being bitchy because he was getting cold.  
"Were you serious before? About prostituting yourself?"

The look in Dean's eyes told him all he needed to know. Sam sighed sadly.

"You don't need to do that. Actually-" Sam paused. "Please _don't_ do that. I don't want you to get sick or hurt from prostituting yourself for money."

Dean looked at Sam, who was watching him intently.  
"Okay." he said, "I won't."

" _Good._ " Sam breathed out a breath he hadn't realized he had been holding in. "Now, could you please play some more? I'd like to get that hot beverage we were pursuing at some point today."

Dean chuckled and obliged Sam, strumming the intro to another rock classic.

* * *

The dark-haired man turned the corner from the parking lot, hands in the pockets of his trench coat as he tried to protect them from the freezing cold.

He heard the music long before he saw the two brothers sitting on the cold cement. He looked up from the pavement and saw the two brothers singing to the music being produced from the old (yet taken care of) guitar.

He walked up to the brothers and opened up his wallet, placing the twenty dollar bill into the case.

He met eyes with the younger brother and nodded at him, and then briskly walked into the coffeehouse to meet his brothers for a cup of coffee like they did every Saturday morning.

Sam watched the man's retreating back in awe. Dean had been to focused on his playing to notice him, but Sam did. And he wanted to thank him.

But first, a warm beverage.


	2. The Past Impacts The Present

**Summary for the Chapter:**

> Castiel was seriously rethinking his life choices.

Castiel sat inside of the coffeehouse, cradling his coffee cup in his hand, letting it warm his palms. He was in deep thought about his life- and was wondering where it went wrong.  
  
At one point in time, he had been his father's favorite son- but then when his brother Michael had gotten into college for financing; Castiel gave up on trying to win his father over with grandiose gestures.  
  
He decided to start embracing himself- and that meant getting a job at a coffeehouse, working long hours to pass the time.  
  
Discovering himself sexually, musically, and artistically- if he could draw a straight line.  
  
Castiel had met his friend Crowley one of the first days he started working at the shop- either because Castiel was a new employee, or because he stuck out like a sore thumb with his 'I'm forcing myself to be here' attitude and his ruffled hair.  
  
Either way, Crowley was saving up for a car so he could-and quote- "Drive away from my problems instead of walking or running away from them."  
  
Both of them- Castiel at age 20, Crowley at age 21- had found the coffeehouse to work in.  
  
It's been two years since they started.  
  
But since that time, much has changed.  
  
First, Crowley's father passed away- leaving him a family business to maintain, as well as hordes of wealth.  
  
  
Castiel is almost as well off.  
  
  
He realized about a year ago that what he really wanted to do was write novels, so he quit his job after saving enough money to buy a laptop- and he got started right away.  
  
He published it; and- even with the great success of his first novel, Castiel still didn't feel right.  
  
He felt as if something were missing. Like he was empty on the inside.  
  
And for his emptiness, he knew no solution.  
_________________________________  
  
And so, every Saturday (as it was instilled a ritual since Crowley's father passed) - Castiel meets with his brothers Lucifer, Michael, and Gabriel in the coffee shop.  
  
Sometimes Crowley joins them- sometimes he doesn't- (he's unpredictable like the weather).  
  
The sound of the door opening and the shuffling of feet on the tiled floor drew Castiel out of his stupor.  
  
He looked up, ready to greet his brothers or Crowley- but instead locked eyes with the most handsome man he had ever seen.  
  
Castiel breathed a sharp intake of air, and gulped down some of his scorching hot coffee.  
  
The man blinked, and looked away from Castiel- pointing his emerald-green eyes towards the menu.  
  
He cleared his throat before saying, "Can I please get a large black coffee?"  
  
The girl manning the counter studied at him for a moment before saying, "Sure. That'll be $2.80."  
  
The guy took a bill from his pocket and placed it on the counter. The door opened again.  
  
"Hey, Cassieboo!" A voice called, bringing Castiel out of his trance.  
  
"My god, Crowley- don't call me that." Castiel said, exhaustedly.  
  
The man at the counter had received his change, and was headed out the door.  
  
He had an expression on his face that could only be construed as exhaustion; and he was wearing it with pride.  
  
Outside, he sat down next to his brother on the pavement- handing the coffee to him after taking a throat-warming swig; wincing at the feeling of the scalding coffee burn his throat.  
  
"So, what's new?" he asked Sam.


	3. Possibilities a' Plenty

**Summary for the Chapter:**

> A mysterious stranger approaches Sam and Dean with a flyer and a golden opportunity.

"So, what's new?" Dean asked tiredly.

Sam looked over at his brother, and yawned before saying, "Made thirty dollars from some Slipknot."

Dean fixed him with a look of disbelief. "Which song?"

"Psychosocial." Sam answered, and then he took a careful swallow from the shared coffee. "Played, too."

"Yeah?" Dean leaned his head back against the wall.

"Yeah." Sam said quietly. "The dude was a fan, apparently."

"And apparently a great tipper." Dean added helpfully.

Sam nodded. "That too."

They sat that way for a couple more minutes, passing the coffee between the two of them- attempting to warm themselves up in the bitter cold.

It wasn't helping very much.

Sam stuck his gloved hands in his pockets and tucked his face down further into his scarf. Dean looked over at him, his eyebrows raised with concern.

"I'm fine, Dean." Sam said, waving him off, "It's just cold out here, that's all. Scout's honor." He held up his hand in mock salute.

"Hey, you can't do that- you weren't a Boy Scout!" Dean said.

"It's just an expression." Sam said, utterly confused.

"Not when you use it like that," Dean replied.

"I'm pretty sure its still used as an expression, no matter what.." Sam trailed.

Dean sighed, and took another swig of coffee. It had cooled considerably just by sitting outside in the cold for five minutes, and was now drinkable. Well, drinkable without getting scalded.

"I can never win with you, can I?" Dean thought aloud.

"Nope." Sam said with a smile.

"Damn."

They sat next to each other in comfortable silence, the occasional passerby tossing a dollar or two into their open guitar case.

As Sam finished off the dregs of the coffee, Dean had picked up the guitar and started strumming out the beginning chords of AC/DC's "Highway to Hell"- which sounded a lot different when played on an acoustic guitar, to an electric like the original.

A man in a dusty-brown jacket rounded the corner, his head down and his hands in his pockets. He looked up long enough to make eye contact with both of the brothers.

The man gave them a small smile, and said, "Hi."

"Hey." Sam replied, warily.

"There's a place a little ways away from here, maybe two blocks, that's looking for some help- if you're looking to earn some money." The man said. He handed Sam a slip o paper. "Basically, they need somebody to do the dishes and mop up the floors."

A smile was forming upon Sam's face as he thought of the different scenarios if he were to get this job.

He looked up to thank the man for giving him the flier- but he was already gone from view.


	4. Ice Sculpture

**Summary for the Chapter:**

> Dean is worried about Sam.  
> * * * * *  
> "Yeah, Dean?" Sam replied, wiping his nose on the back of his hoodie's sleeve. Dean wrinkled his nose, but didn't say anything about it. (They'd just need to do a run to the laundromat some time within the next week.)

**Notes for the Chapter:**

> SO SORRY about the wait, I've got alot of stuff going on right now (school, family issues, etc.. you've heard it all before.) But I mean- I just saw my sister for the first time in almost two months!!
> 
> Super psyched- I know know what her baby's name is! (She doesn't have a middle name set in stone, but. Whatever.)  
> The baby's name is Elizabeth! And I'mma be an aunt!! :D

Sam tucked the flier into his pocket and turned to Dean, a grin brightening his face. "I'm gonna try it."

Dean made a puzzled face. "Try what?"

"To get a job." Sam said. "Did you _not_  just hear that conversation?"

"Heard about half of it."

"And?"

"I dunno, Sammy- some guy walking up to you in the middle of a cold, midwinter's day- and handing you a flier and then telling you that he's got work for you isn't the _least_ _bit_ suspicious?" Dean replied sarcastically.

Sam looked at his brother with wonder. "How do you do that?"

"Do what?"

"Say so much without stopping to think about how what you're saying might affect people," Sam paused, "Or maybe stop to breathe."

Dean shrugged. "It's a skill I've learned to master."

Sam huffed. "Well, it's not very appealing."

Raising an eyebrow, Dean said, "Oh, really?"

"Yes, really. It's obnoxious."

The frigid wind blew, rustling the loose papers and plastic bags that littered the sidewalk. Sam tucked his hands deeper into his coat pocket with a shiver.

Dean didn't notice the microscopic shake of his brother's shoulders as they sat in the cold. "Bitch." The older responded, an upward twist to his lips present.

Sam pulled a face at that. "Jerk."

Dean grinned, and scooted closer to his 'little' brother for warmth. It was cold out, after all- and he didn't want either of them to get sick, because even cold medicine was getting expensive. He had no idea what he was going to do if one of them ever _did_ get sick.

But he'd rather not find out.

"Hey, Sam." He said, bringing his brother out of his library book.

"Yeah, Dean?" Sam replied, wiping his nose on the back of his hoodie's sleeve. Dean wrinkled his nose, but didn't say anything about it. (They'd just need to do a run to the laundromat some time within the next week.)

"It's getting cold out here," Dean suggested, "We should probably go somewhere warmer so we don't catch hypothermia or something."

"Yeah, that's probably a good idea." Sam shut his book, and tucked it under his arm. Dean collected the money from the bottom of the guitar case and put it in a Ziploc bag. Sam carefully placed Dean's guitar into the case, and closed it up with the latches.

Dean took the strap on the case and swung it over his shoulder.

"Let's go." he said, and he and Sam made their way back to the Impala for some well deserved rest. Their sleeping bags and pillows were stowed away in the trunk, and Dean was exhausted enough to fall asleep standing up like a horse- with or without one.

But Sam didn't look too good, and when Dean had huddled up to him for warmth- he had found that his brother was practically an ice sculpture under the two hoodies that Dean forced him to wear today.

And it concerned him.

**Notes for the Chapter:**

> Thank you SO much for reading this and for stickin' around for so long!  
> You guys rock!! :)

**Author's Note:**

> So? What'd ya think?  
> (Comments are amazing little gifts that I'd LOVE to receive!!)
> 
> (Big thanks to those who read this: next chapter will be up soon!!)
> 
> This HIGHFIVE is for you!!!:
> 
> /(^_^)/\\(^_^)\


End file.
